4-[4-chlorobenzyl-((E)-4,4,4-trifluoro-3-oxo-but-1-enyl)amino]benzenesulfonamide | 1135241-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-chlorobenzyl-((E)-4,4,4-trifluoro-3-oxo-but-1-enyl)amino]benzenesulfonamide
• 英文别名: 4-[(4-chlorophenyl)methyl-[(E)-4,4,4-trifluoro-3-oxobut-1-enyl]amino]benzenesulfonamide
• CAS: 1135241-05-2
• 化学式: C₁₇H₁₄ClF₃N₂O₃S
• 分子量: 418.824
• InChiKey: FHZADBSEPBDCSW-MDZDMXLPSA-N

物化性质

• 沸点：
  514.0±60.0 °C(predicted)
• 密度：
  1.466±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-(4-氯苄基氨基)苯磺酰胺 、 1,1,1-trifluoro-4-iso-butoxy-3-buten-2-one 以 乙腈 为溶剂， 反应 16.0h， 以78%的产率得到4-[4-chlorobenzyl-((E)-4,4,4-trifluoro-3-oxo-but-1-enyl)amino]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and carbonic anhydrase I, II, IX and XII inhibition studies of 4-N,N-disubstituted sulfanilamides incorporating 4,4,4-trifluoro-3-oxo-but-1-enyl, phenacylthiourea and imidazol-2(3H)-one/thione moieties

  摘要：

  A series of sulfonamides incorporating the sulfanilamide ( SA) scaffold were prepared. Reaction of the 4-amino moiety of SA with benzyl chlorides or substituted bromoacetophenones afforded the derivatives which were then reacted with 1,1,1-trifluoro-4-isobutoxybut-3-en-2-one leading to a series of 4-N,N-disubstituted SAs. The key intermediates were also reacted with ethoxycarbonyl isothiocyanate leading to thioureas or were cyclized in the presence of potassium cyanate/isothiocyanate to the corresponding imidazol-2(3H)-one/thiones. The new compounds were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and the transmembrane, tumor-associated CA IX and XII. These sulfonamides were ineffective CA I and II inhibitors but were nanomolar CA IX and XII inhibitors, making them of interest as clinical candidates for antitumor/antimetastasis applications. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.030

文献信息

• Synthesis and carbonic anhydrase I, II, IX and XII inhibition studies of 4-N,N-disubstituted sulfanilamides incorporating 4,4,4-trifluoro-3-oxo-but-1-enyl, phenacylthiourea and imidazol-2(3H)-one/thione moieties
  作者：Cenzo Congiu、Valentina Onnis、Gianfranco Balboni、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.02.030

  日期：2014.4

  A series of sulfonamides incorporating the sulfanilamide ( SA) scaffold were prepared. Reaction of the 4-amino moiety of SA with benzyl chlorides or substituted bromoacetophenones afforded the derivatives which were then reacted with 1,1,1-trifluoro-4-isobutoxybut-3-en-2-one leading to a series of 4-N,N-disubstituted SAs. The key intermediates were also reacted with ethoxycarbonyl isothiocyanate leading to thioureas or were cyclized in the presence of potassium cyanate/isothiocyanate to the corresponding imidazol-2(3H)-one/thiones. The new compounds were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and the transmembrane, tumor-associated CA IX and XII. These sulfonamides were ineffective CA I and II inhibitors but were nanomolar CA IX and XII inhibitors, making them of interest as clinical candidates for antitumor/antimetastasis applications. (C) 2014 Elsevier Ltd. All rights reserved.